The Cyano Group as a Traceless Activation Group for the Intermolecular [3+2] Cycloaddition of Azomethine Ylides: A Five‐Step Synthesis of (±)‐Isoretronecanol |
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| Authors: | Jundong Li Huaibo Zhao Xunjin Jiang Xiance Wang Haiming Hu Lei Yu Prof?Dr Yandong Zhang |
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| Affiliation: | Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China) |
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| Abstract: | The cyano group was used as a traceless activation group for the 3+2] cycloaddition of azomethine ylides in a two‐step process, thereby providing a highly effective approach to 5‐unsubstituted pyrrolidines. The transformation includes the silver acetate catalyzed intermolecular 1,3‐dipolar cycloaddition of α‐iminonitriles and an unprecedented sodium borohydride induced reductive decyanation reaction. A diverse array of substrates is amenable to this transformation. The methodology was further extended to a five‐step total synthesis of the pyrrolizidine natural product isoretronecanol. |
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| Keywords: | cycloaddition pyrrolidines reductive decyanation total synthesis traceless activation |
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